Stabilization and hydrogenation methods for microbial-derived olefins

Patent metadata

Field	Value
Publication number	US-10183901-B2
Application number	US-201715458907-A
Country	US
Kind code	B2
Filing date	Mar 14, 2017
Priority date	Apr 2, 2009
Publication date	Jan 22, 2019
Grant date	Jan 22, 2019

Abstract

Methods and compositions for stabilization and subsequent hydrogenation of a microbial-derived immiscible olefin are described. The methods comprise separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin thereby forming a crude olefin composition; purifying the crude olefin composition thereby forming a purified olefin composition; and adding a phenolic antioxidant to the purified olefin composition wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise reacting the purified olefin composition with hydrogen in the presence of a hydrogen catalyst such that hydrogen saturates at least one double bond in the olefin. Hydrogenated compositions produced by the methods are further provided.

First claim

What is claimed is:

1. A hydrogenated composition derived from a microbial derived olefin composition, the hydrogenated composition produced by a method comprising:
(a) separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin, thereby forming a crude olefin composition;
(b) purifying the crude olefin composition thereby forming a purified olefin composition;
(c) adding a phenolic antioxidant to the purified olefin composition to form a stabilized purified microbial-derived olefin composition, wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents, and is present in an amount that is at least 0.0001% by weight of stabilized purified microbial-derived olefin composition; and
(d) reacting the stabilized purified microbial-derived olefin composition with hydrogen in the presence of a hydrogenation catalyst at a temperature at or greater than about 20° C. such that hydrogen saturates at least one double bond in the olefin, thereby producing the hydrogenated composition.

2. The hydrogenated composition of claim 1 , wherein the method further comprises adding a phenolic antioxidant to the crude olefin composition.

3. The hydrogenated composition of claim 1 , wherein the purification step comprises removing or reducing monoglycerides, diglycerides, ergosterol, squalene, or any combination thereof from the crude olefin composition.

4. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is selected from the group consisting of 3-tert-butyl-4-hydroxyanisole; 2-tert-butyl-4-hydroxyanisole; 2,4,-dimethyl-6-tert-butylphenol; and 2,6-di-tert-butyl-4-methylphenol.

5. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is a catechol.

6. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is 4-tert-butyl catechol.

7. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.001% by weight of the stabilized purified microbial-derived olefin composition.

8. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.005% by weight of the stabilized purified microbial-derived olefin composition.

9. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.01% by weight of the stabilized purified microbial-derived olefin composition.

10. The hydrogenated composition of claim 1 , wherein the hydrogenation reaction occurs at a temperature that is greater than about 100° C.

11. The hydrogenated composition of claim 1 , wherein the hydrogenated composition comprises a partially hydrogenated immiscible olefin.

12. The hydrogenated composition of claim 1 , wherein the microbial-derived olefin is a C 5 -C 20 isoprenoid.

13. The hydrogenated composition of claim 1 , wherein the microbial-derived olefin is a C 10 -C 15 isoprenoid.

14. The hydrogenated composition of claim 1 , wherein the stabilized purified microbial-derived olefin comprises farnesene in at least about 50%, 60%, 70%, 80%, 90%, 93%, 95%, 97%, 99% or greater by weight of the immiscible olefin.

15. The hydrogenated composition of claim 14 , wherein the hydrogenation reaction comprises selective hydrogenation of farnesene to reduce one, two, three, or four double bonds in farnesene.

16. The hydrogenated composition of claim 15 , wherein farnesene is selectively hydrogenated to reduce one double bond.

17. The hydrogenated composition of claim 15 , further comprising bisabolane in an amount that is equal to or greater than 0.1% by weight of the hydrogenated composition.

18. A hydrogenated composition derived from a microbial-derived olefin composition, the hydrogenated composition produced by a method comprising:
reacting a stabilized purified microbial-derived olefin composition with hydrogen in the presence of a hydrogenation catalyst, wherein the stabilized purified microbial-derived olefin composition comprises:
(a) farnesene in an amount that is at least equal to or greater than about 90% by weight of the stabilized purified microbial-derived olefin composition;
(b) bisabolene in an amount that is equal to or greater than about 0.1% by weight of the stabilized purified microbial-derived olefin composition;
(c) zingibrene in an amount that is equal to or greater than about 0.1% by weight of the stabilized purified microbial-derived olefin composition; and
(d) a phenolic antioxidant, wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents in an amount that is at least about 0.005% by weight of the stabilized purified microbial-derived olefin composition,
wherein the hydrogenation reaction saturates at least one double bond in farnesene.

19. The hydrogenated composition of claim 18 , wherein the hydrogenated composition further comprises at least about 0.1% bisabolane by the weight of the hydrogenated composition.

20. The hydrogenated composition of claim 18 , wherein the hydrogenated composition comprises a partially hydrogenated farnesene.

Assignees

• Amyris Inc

Inventors

• Ohler Nicholas L
• Vazquez Roberto

Classifications

• C07C7/20

  Use of additives, e.g. for stabilisation · CPC title

• Y02P30/20

  using bio-feedstock · CPC title

• C07C11/21

  Alkatrienes; Alkatetraenes; Other alkapolyenes · CPC title

• C07C2523/755

  Nickel · CPC title

• C10L1/04

  essentially based on blends of hydrocarbons · CPC title